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Amides and Flavonoids from the Fruit and Leaf Extracts of <i>Melodorum siamensis</i>

By Wuttichai Jaidee (6273284), Raymond J. Andersen (155984), Miguel A. G. Chavez (6273287), Yan A. Wang (6273290), Brian O. Patrick (155965), Stephen G. Pyne (1403101), Chatchai Muanprasat (285849), Suparerk Borwornpinyo (3509102) and Surat Laphookhieo (1647802)

Abstract

Four new chalcones (<b>1</b>, <b>10</b>, <b>13</b>, and <b>14</b>), a new flavanone, (<b>9</b>), a new amide (<b>8</b>), and 19 known compounds were acquired from <i>Melodorum siamensis</i>. The structures were established by NMR and MS data analyses. Compounds <b>1</b> (er 1.4:1) and <b>2</b> (er 1.1:1) were scalemic and were resolved to yield (−)-<b>1</b> and (+)-<b>1</b> and (−)-<b>2</b> and (+)-<b>2</b>, respectively. The absolute configurations of these compounds were determined from experimental and calculated ECD data. The structures and configurations of (−)-<b>2</b> and (+)-<b>8</b> were identified by single-crystal X-ray diffraction analysis. Compound <b>11</b> showed nuclear factor-κB inhibitory effects (IC<sub>50</sub> = 9 μM) in a pancreatic β cell line (MIN-6 cells)

Topics: Biochemistry, Medicine, Cell Biology, Pharmacology, Sociology, Developmental Biology, Inorganic Chemistry, Hematology, Plant Biology, Environmental Sciences not elsewhere classified, Biological Sciences not elsewhere classified, Chemical Sciences not elsewhere classified, MS data analyses, IC, Flavonoid, ECD, MIN -6 cells, 9 μ M, Compound, factor, -κB, Amide, Extracts, scalemic, compound, configuration, chalcone, single-crystal X-ray diffraction analysis, flavanone, NMR, amide, pancreatic β cell line, Melodorum siamensis
Year: 2019
DOI identifier: 10.1021/acs.jnatprod.8b00696.s002
OAI identifier: oai:figshare.com:article/7643234
Provided by: FigShare
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